Old Friends is a three-disc compilation of original album tracks, as well as 15 previously unreleased tracks and one B-side.  For those wondering about the weird order in which the songs appear, they're on here according to their recording dates. The title of the set, is taken from the song by the same name on the Bookends album as well as Disc 3 of this set.

43 of the tracks on Old Friends are album cuts. The remaining 16 tracks can be broken down as follows:

• 1 B-side
  • Disc 2, Track 18: "You Don't Know Where Your Interest Lies" (recorded 6/14/67; released as the B-side of "Fakin' It" from the Bookends album)
• 2 unissued demos
  • Disc 1, Track 1: "Bleeker Street" (recorded 3/10/64; demo from the Wednesday Morning, 3 a.m. sessions)
  • Disc 3, Track 9: "Feuilles-O" (recorded 8/11/69; demo from the Bridge Over Troubled Water sessions)
• 3 unissued studio recordings
  • Disc 1, Track 16: "Blues Run The Game" (recorded 12/21/65; previously unissued outtake from the Sounds Of Silence sessions)
  • Disc 2, Track 20: "Comfort and Joy" (recorded 4/19/67; previously unissued Christmas recording)
  • Disc 2, Track 21: "Star Carol" (recorded 4/19/67; previously unissued Christmas recording)
• 10 unissued live recordings
  • Disc 2, Track 10: "A Poem On The Underground Wall" (recorded 1/22/67 at Lincoln Center)
  • Disc 2, Track 11: "Red Rubber Ball" (recorded 1/22/67 at Lincoln Center)
  • Disc 2, Track 12: "Blessed" (recorded 1/22/67 at Lincoln Center)
  • Disc 2, Track 13: "Anji" (recorded 1/22/67 at Lincoln Center)
  • Disc 2, Track 14: "A Church Is Burning" (recorded 1/22/67 at Lincoln Center)
  • Disc 3, Track 3: "Overs" (recorded 10/13/68 at Memorial Auditorium in Burlington, Vermont)
  • Disc 3, Track 4: "A Most Peculiar Man" (recorded 10/13/68 at Memorial Auditorium in Burlington, Vermont)
  • Disc 3, Track 5: "Bye Bye, Love" (recorded 10/13/68 at Memorial Auditorium in Burlington, Vermont)
  • Disc 3, Track 17: "Hey Schoolgirl"/"Black Slacks" (recorded 11/28/69 at Carnegie Hall)
  • Disc 3, Track 18: "That Silver Haired Daddy Of Mine" (recorded 11/28/69 at Carnegie Hall)